S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid

• CAS: 127985-74-4
• Catalog Number: ACM127985744
• Category: Main Products
• Molecular Weight: 687.8
• Molecular Formula: C24H33N5O8S·2.5HCl·2.5H₂O
• Synonyms: p-SCN-Bn-DOTA
• Appearance: Solid

Case Study

p-SCN-Bn-DOTA- and p-SCN-Bn-DTPA-rituximab Lyophilized Formulations for NHL Radioimmunotherapy

Darinka Gjorgieva Ackova, et al. Iranian Journal of Pharmaceutical Research: IJPR, 2016, 15(3), 295.

This work compared and physicochemically evaluated immunoconjugates prepared with p-SCN-Bn-DOTA and p-SCN-Bn-DTPA as bifunctional chelators (BFCAs) conjugated to rituximab. The results showed that the antibody structure of the rituximab immunoconjugates were preserved, with an average of 6.1 p-SCN-Bn-DOTA and 8.8 p-SCN-Bn-DTPA groups per antibody molecule, supporting the possibility of imaging/therapy for non-Hodgkin lymphoma (NHL).
Preparation of rituximab immunoconjugates
· BFCAs (p-SCN-Bn-DOTA and p-SCN-Bn-DTPA) were dissolved in 0.1 M PBS (pH 8.0) to a final concentration of 10 mg/mL.
· The calculated amount of BFCA needed to achieve a 20-fold molar excess over Rituximab (10 mg/mL) was added to the purified monoclonal antibody in 0.1 M PBS (pH 8.0). The mixture was then left to incubate overnight at 4 °C with gentle shaking.
· To purify the conjugates, ultrafiltration was conducted, washing the immune conjugates with 0.05 M ammonium acetate, pH 7.0, until the absorbance at 280 nm of the ultrafiltrate approached zero, indicating the absence of unbound chelating agent in the immune conjugate solution.

p-SCN-Bn-DOTA for the Preparation of ¹⁷⁷Lu-DOTA-DN(PTX)-BN Drug and Radiation Delivery Nanosystem

Gibbens-Bandala, Brenda, et al. Polymers, 2019, 11(10), 1572.

A novel drug and radiation delivery nanosystem (¹⁷⁷Lu-DOTA-DN(PTX)-BN) based on ¹⁷⁷Lu labeled polyamidoamine (PAMAM) dendrimer (DN), loaded with paclitaxel (PTX) and functionalized on the surface with Lys¹Lys³(DOTA)-bombesin (BN) peptide was successfully prepared to specifically target the gastrin-releasing peptide receptor (GRPr) overexpressed on breast cancer cells.
Preparation procedure of ¹⁷⁷Lu-DOTA-DN(PTX)-BN
· Firstly, DOTA-DN was prepared by dissolving PAMAM dendrimer and DOTA (p-SCN-Bn-DOTA) in bicarbonate buffer, incubating the mixture, and then purifying and lyophilizing the product.
· Then, for the preparation of DOTA-DN-BN, carboxylate groups activation from Lys¹Lys³(DOTA)-bombesin was achieved by incubating the peptide with HATU at room temperature, followed by the addition of DOTA-DN to the solution with active peptide, and subsequent purification and drying under vacuum. The purpose of DOTA-DN-BN was to reach the GRP receptor using Lys¹Lys³(DOTA)-bombesin as the biomolecule with DOTA as the linker.
· Additionally, Paclitaxel-loaded DN was prepared by mixing DOTA-DN-BN with Paclitaxel, stirring the mixture, and purifying the PTX-loaded dendrimers.
· Once these dendrimeric systems were prepared, they were radiolabeled through the bifunctional chelator DOTA with ¹⁷⁷Lu. The radiolabeling process involved adding a ¹⁷⁷LuCl₃ solution to the dendrimeric systems and incubating each solution at 37 °C for 1 hour.

Custom Q&A

What is the molecular formula of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The molecular formula is C24H33N5O8S.

What are the synonyms for S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The synonyms are (p-SCN-Bn)-dota, 127985-74-4, p-SCN-Bn-DOTA, p-SCN-Bz-dota, and UNII-13KT123BYW.

What is the molecular weight of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The molecular weight is 551.6 g/mol.

When was S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid created?

It was created on October 25, 2006.

When was S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The IUPAC name is 2-[4,7,10-tris(carboxymethyl)-6-[(4-isothiocyanatophenyl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid.

What is the InChI code for S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The InChI code is InChI=1S/C24H33N5O8S/c30-21(31)13-26-5-6-27(14-22(32)33)9-10-29(16-24(36)37)20(12-28(8-7-26)15-23(34)35)11-18-1-3-19(4-2-18)25-17-38/h1-4,20H,5-16H2,(H,30,31)(H,32,33)(H,34,35)(H,36,37).

What is the InChIKey of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The InChIKey is UDOPJKHABYSVIX-UHFFFAOYSA-N.

What is the canonical SMILES representation of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The canonical SMILES representation is C1CN(CCN(C(CN(CCN1CC(=O)O)CC(=O)O)CC2=CC=C(C=C2)N=C=S)CC(=O)O).

What is the CAS number of S-2-(4-Isothiocyanatobenzyl)-1,4,7,10-tetraazacyclododecane tetraacetic acid?

The CAS number is 127985-74-4.